Metathesis Catalysts. V. Competitive Character of Metathesis and Alkylation Reactions Catalyzed by Tungsten Hexachloride-Ethylaluminum Dichloride

Hocks, Léonard; Noels, Alfred; Hubert, André J.; Teyssié, Philippe

doi:10.1021/jo00871a033

Article (Scientific journals)

Metathesis Catalysts. V. Competitive Character of Metathesis and Alkylation Reactions Catalyzed by Tungsten Hexachloride-Ethylaluminum Dichloride

Hocks, Léonard; Noels, Alfred; Hubert, André J. et al.

1976 • In Journal of Organic Chemistry, 41 (9), p. 1631-1635

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/236095

DOI
10.1021/jo00871a033

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

TEYSSIE_13.pdf

Publisher postprint (1.54 MB)

Download

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Abstract :

[en] The olefin metathesis catalytic system WCl6-EtAlCl2 in an aromatic solvent promotes both olefin metathesis and solvent alkylation reactions. The yields of these two competitive reactions strongly depend on the relative concentration of the three compounds of the system (olefin, solvent, catalyst), with a marked dependence on the π donor ability of the aromatic solvent; moreover, our catalytic conditions can promote exclusive formation of monosubstituted benzenes at the thermodynamic equilibrium. The mechanism proposed involves competitive coordination equilibria of the solvent and of the olefin as the key step. © 1976, American Chemical Society. All rights reserved.

Disciplines :

Chemistry

Author, co-author :

Hocks, Léonard ; Laboratoire de Chimie Macromoléculaire et de Catalyse Organique, Université de Liège, Sart Tilman par 4000, Liège, Belgium

Noels, Alfred ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)

Hubert, André J.

Teyssié, Philippe ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)

Language :

English

Title :

Metathesis Catalysts. V. Competitive Character of Metathesis and Alkylation Reactions Catalyzed by Tungsten Hexachloride-Ethylaluminum Dichloride

Publication date :

1976

Journal title :

Journal of Organic Chemistry

ISSN :

0022-3263

eISSN :

1520-6904

Publisher :

American Chemical Society, Washington, United States - District of Columbia

Volume :

Issue :

Pages :

1631-1635

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 29 May 2019

Statistics

Number of views

23 (1 by ULiège)

Number of downloads

136 (1 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

Bibliography

N. Calderon, H. Y. Chen, and K. W. Scott, Tetrahedron Lett., 3327 (1967).
N. Calderon, E. A. Ofstead, J. P. Ward, W. A. Judy, and R. W. Scott, J. Am. Chem. Soc., 90, 4133 (1968).
N. Calderon, E. A. Ofstead, and W. A. Judy, J. Polym. Sci., 5, 2209 (1967).
K. W. Scott, N. Calderon, E. A. Ofstead, W. A. Judy, and J. P. Ward, Adv. Chem. Ser., 91, 399 (1969).
P. Günter, F. Haas, G. Marwede, K. Nützel, W. Oberklrch, G. Pampus, J. Witte, and N. Schön, Angew. Makromol. Chem., 16/17, 27 (1971).
G. Dall'Asta, G. Stigliani, A. Greco, and L. Motta, Polym. Prepr., 13, 910 (1972).
G. Dall'Asta and G. Motroni, Chim. Ind. (Milan), 50, 972 (1968).
V. M. Kothari and J. J. Tazuma, Chem. Eng. News, 48, 39 (1970).
V. M. Kothari and J. J. Tazuma, J. Org. Chem., 36, 2951 (1971).
A. Uchida, Y. Hamano, Y. Mukai, and S. Matsuda, Ind. Eng. Chem., Prod. Res. Dev., 10, 372 (1971).
L. Hocks, A. J. Hubert, and P. Teyssié, Tetrahedron Lett., 3687 (1972).
V. P. Yur'Ev, G. A. Gailyunas, G. A. Tolstikov, V. I. Khostenko, and S. R. Rafikov, Dokl. Chem., 219, 844 (1974).
F. W. McLafferty, “Mass Spectrometry”, W. A. Benjamin, New York, N.Y., 1966.
L. Hocks, A. J. Hubert, and P. Teyssié, Tetrahedron Lett., 2719 (1973).
L. Hocks, A. J. Hubert, and P. Teyssié, Tetrahedron Lett., 877 (1974).
A. F. Popov, N. N. Korneev, and G. S. Solov'eva, Sov. Chem. Ind. (Engl. Transl.), 48, 71 (1972).
E. L. Muetterties, Inorg. Chem., 14, 951 (1975).
L. Hocks, Bull. Soc. Chim. Fr., 1893 (1975).
W. B. Hughes, Adv. Chem. Ser, 132, 192 (1974).
H. Höcker and F. R. Jones, Makromol. Chem., 161, 251 (1972).
R. J. Maine and G. J. Leigh, Chem. Soc. Rev., 4, 155 (1975).
I. W. Stolz, G. R. Dobson, and R. K. Sheline, Inorg. Chem., 2, 1264 (1963).
M. Wrighton, G. S. Hammond, and H. B. Gray, J. Am. Chem. Soc., 92, 6068 (1970).
M. Wrighton, G. S. Hammond, and H. B. Gray, J. Am. Chem. Soc., 93, 6048 (1971).
B. T. Manuel and F. G. A. Stone, Chem. Ind. (London), 1349 (1959).
I. W. Stolz, H. Haas, and R. K. Sheline, J. Am. Chem. Soc., 87, 716 (1965).
H. F. Priest and W. C. Schumb, J. Am. Chem. Soc., 70, 2291 (1948).
H. J. Clase, A. M. Noble, and J. M. Winfried, Spectrochim. Acta, Part A, 25, 293 (1969).
J. C. Evans and G. Y. S. Lo, J. Mol. Spectrosc., 26, 147 (1968).
F. N. Tebbe and E. L. Muetterties, Inorg. Chem., 7, 172 (1968).
R. A. Walton, P. C. Crouch, and B. J. Brisdon, Spectrochim. Acta, Part A, 24, 601 (1968).
C. K. Jorgensen, Mol. Phys., 2, 309 (1959).
C. K. Jorgensen, Top. Curr. Chem., 56, 1 (1975).
Y. Marcus and I. Ellezer, Coord. Chem. Rev., 4, 273 (1969).
A. Clark and C. Cook, J. Catal., 15, 420 (1969).
W. B. Hughes, J.Am. Chem. Soc., 92, 532 (1970).
A. J. Moffat and A. Clark, J. Catal., 17, 264 (1970).
G. A. Olah and P. v. R. Schleyer, “Carbonium Ions”, Vol. II, Interscience, New York, N.Y., 1968, pp 774-776.
C. R. Smoot and H. C. Brown, J. Am. Chem. Soc., 78, 2185, 6245 (1956).
C. P. Casey and J. J. Burkhardt, J. Am. Chem. Soc., 96, 7808 (1974).
T. J. Katz and J. M. Ginnis, J. Am. Chem. Soc., 97, 1592 (1975).
R. H. Grubbs, P. L. Burk, and D. D. Carr, J. Am. Chem. Soc., 97, 3265 (1975).
J. L. Herisson and Y. Chauvin, Makromol. Chem., 141, 161 (1970).
J. P. Soufflet, D. Commereuc, and Y. Chauvin, C. R. Acad. Sci., Ser. C, 276, 169 (1973).
H. R. Alul, J. Org. Chem., 33, 1522 (1968).
C. D. Nenitzescu, Rev. Roum. Chim., 9, 5 (1964).
R. D. Gilliom, “Introduction to Physical Organic Chemistry”, Addison-Wesley, Reading, Mass., 1970, p 227.
J. L. Andrews, Chem. Rev., 54, 713 (1954).
J. Hine, “Physical Organic Chemistry”, 2d ed, McGraw-Hill, New York, N.Y., 1962, p 344.